Julichrome derivatives and gliotoxin from a soil derived <i>Streptomyces</i> sp.

Shen, Tong; Li, Le-Mei; Xu, Zeyu; Wang, Yongdong; Xie, Wenrui

doi:10.1080/14786419.2019.1611814

Cited by 10 publications

(9 citation statements)

References 15 publications

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“…In summary, 11 secondary metabolites including two new julichrome monomers, julichromes Q 11 (1) and Q 12 (2), were isolated and characterized from Batillaria zonalis-associated S. sampsonii SCSIO 054. X-ray crystallographic analysis of compound 4 revealed its absolute configuration and facilitated the revision of absolute configuration from (9R) to (9S) in the julichrome family.…”

Section: Discussionmentioning

confidence: 99%

“…Biodiversity 2020, 17, e2000057 www.cb.wiley.com (2 of 9) e2000057 © 2020 Wiley-VHCA AG, Zurich, Switzerland compounds 1-11. Compounds 3 -11 were identified as julichromes Q 10 (3), [12] Q 3 · 5 (4), [4] Q 3 · 3 (5), [7] Q 6 · 6 (6), [7] Q 6 (7), [4] chrysophanol (8), [13] 4-acetylchrysophanol (9), [4] islandicin (10), [14] and huanglongmycin A (11) [15] on the basis of MS, 1 H-and 13 C-NMR spectroscopic analyses and subsequent comparisons to previously published datasets. Julichrome Q 11 (1) was obtained as yellowish oil.…”

Section: Structural Elucidationmentioning

confidence: 99%

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Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q_3 ⋅ 5 and Q_3 ⋅ 3

Dong

Ding

Sun

et al. 2020

Chemistry & Biodiversity

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Two julichrome monomers, julichromes Q 11 (1) and Q 12 (2), along with five known julichromes (Q 10 , Q 3 · 5 , Q 3 · 3 , Q 6 · 6 , Q 6 , 3 -7) and four known anthraquinones (chrysophanol, 4-acetylchrysophanol, islandicin, huanglongmycin A, 8-11), were isolated from the marine gastropod mollusk Batillaria zonalis-associated Streptomyces sampsonii SCSIO 054. This is the first report of julichromes isolated from a marine source. Extensive dissection of 1D and 2D NMR datasets combined with X-ray crystallography enabled rigorous elucidation of the previously reported configurations of julichrome Q 3 · 5 (4) and related julichrome Q 3 · 3 (5); both of the configuration at C(9) needs to be revised. In addition, julichrome Q 12 (2) was found to display antibacterial activity against Micrococcus luteus and Bacillus subtilis with MICs of 2.0 and 8.0 μg mL À 1 ; four compounds (1, 3, 6, 7) also showed inhibitory activities against an array of methicillin-resistant Staphylococcus aureus, S. aureus and S. simulans AKA1 with MIC values ranging from 8 to 64 μg mL À 1 . Figure 4. Single-crystal X-ray structure of 4 (ORTEP drawing, ellipsoid probability 30 %).

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Section: Discussionmentioning

confidence: 99%

Section: Structural Elucidationmentioning

confidence: 99%

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q_3 ⋅ 5 and Q_3 ⋅ 3

Dong

Ding

Sun

et al. 2020

Chemistry & Biodiversity

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“…The planar structure of 7 is supported by HMBC correlations from H-10 to C-11 (δ C 208.5) as well as those from H 3 -13 (δ H 1.24) to C-2 (δ C 48.1), C-3 (δ C 71.0), C-4 (δ C 61.9), and C-11 (Figure and Table ). The 1D and 2D 1 H and 13 C{ 1 H} NMR spectra of 7 thus resemble those of julichrome Q 10 , which was recently isolated from terrestrial or marine-derived Streptomyces . , …”

Section: Results and Discussionmentioning

confidence: 77%

Discovery of a DNA Topoisomerase I Inhibitor Huanglongmycin N and Its Congeners from Streptomyces sp. CB09001

et al. 2021

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Huanglongmycin (HLM) congeners G−N (7−14) were isolated from Streptomyces sp. CB09001. Among them, 10− 12 possesses a tricyclic scaffold with benzene-fused pyran/pyrone, confirmed by X-ray single crystal diffraction analysis of 12. The structure−activity relationship study of 1, 13, and 14 revealed not only the stronger cytotoxicity of 14 against tested cancer cells but also the critical role of the C-7 ethyl group of 14 in its binding to the DNA−topoisomerase I complex.

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“…Julichrome Q6.6 (Cpd. 378 ) was selectively cytotoxic to SMMC-7721, MCF-7, and MDA-MB-231 cell lines while sparing the L-02 ( Table S3 ) [ 72 ].…”

Section: Resultsmentioning

confidence: 99%

Novel Marine Secondary Metabolites Worthy of Development as Anticancer Agents: A Review

et al. 2021

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Secondary metabolites from marine sources have a wide range of biological activity. Marine natural products are promising candidates for lead pharmacological compounds to treat diseases that plague humans, including cancer. Cancer is a life-threatening disorder that has been difficult to overcome. It is a long-term illness that affects both young and old people. In recent years, significant attempts have been made to identify new anticancer drugs, as the existing drugs have been useless due to resistance of the malignant cells. Natural products derived from marine sources have been tested for their anticancer activity using a variety of cancer cell lines derived from humans and other sources, some of which have already been approved for clinical use, while some others are still being tested. These compounds can assault cancer cells via a variety of mechanisms, but certain cancer cells are resistant to them. As a result, the goal of this review was to look into the anticancer potential of marine natural products or their derivatives that were isolated from January 2019 to March 2020, in cancer cell lines, with a focus on the class and type of isolated compounds, source and location of isolation, cancer cell line type, and potency (IC50 values) of the isolated compounds that could be a guide for drug development.

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Julichrome derivatives and gliotoxin from a soil derived Streptomyces sp.

Cited by 10 publications

References 15 publications

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q_3 ⋅ 5 and Q_3 ⋅ 3

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q_3 ⋅ 5 and Q_3 ⋅ 3

Discovery of a DNA Topoisomerase I Inhibitor Huanglongmycin N and Its Congeners from Streptomyces sp. CB09001

Novel Marine Secondary Metabolites Worthy of Development as Anticancer Agents: A Review

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Julichrome derivatives and gliotoxin from a soil derived Streptomyces sp.

Cited by 10 publications

References 15 publications

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q3 ⋅ 5 and Q3 ⋅ 3

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q3 ⋅ 5 and Q3 ⋅ 3

Discovery of a DNA Topoisomerase I Inhibitor Huanglongmycin N and Its Congeners from Streptomyces sp. CB09001

Novel Marine Secondary Metabolites Worthy of Development as Anticancer Agents: A Review

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Resources

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Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q_3 ⋅ 5 and Q_3 ⋅ 3

Julichrome Monomers from Marine Gastropod Mollusk‐Associated Streptomyces and Stereochemical Revision of Julichromes Q_3 ⋅ 5 and Q_3 ⋅ 3